US1094224A - Process for producing 1,3-diols. - Google Patents

Process for producing 1,3-diols. Download PDF

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Publication number
US1094224A
US1094224A US73810412A US1912738104A US1094224A US 1094224 A US1094224 A US 1094224A US 73810412 A US73810412 A US 73810412A US 1912738104 A US1912738104 A US 1912738104A US 1094224 A US1094224 A US 1094224A
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United States
Prior art keywords
diols
producing
ketone
alcohols
solution
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Expired - Lifetime
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US73810412A
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Lucas Petron Kyriakides
Richard Blair Earle
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Hood Rubber Co
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Hood Rubber Co
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Priority to US73810412A priority Critical patent/US1094224A/en
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    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B3/00—Electrolytic production of organic compounds
    • C25B3/20—Processes
    • C25B3/25—Reduction

Description

UNITED STATES PATENT OFFICE.
LUCAS PETRON KYRIAKIDES AND- RICHARD BLAIR EARLE, OF CAMBRIDGE, MASSA CHUSETTS, ASSIGNORS TO HOOD RUBBER COMPANY, A CORPORATION OF MASSA- Patented Apr. 21, 1914.
CHUSETTS.
PROCESS FOR PRODUCING 1,3-DIOLS.
ll ,094,224. Specification of Letters Patent.
No Drawing.
Application filed December 21, 1912. Serial No. 738,104.
To all whom it may concern Be it known that We, LUCAS P. KYRIAKI- DES and RICHARD B. EARLE, citizens of the United States, residing at Cambridge, Massachusetts, have invented certain new and useful Improvements in Processes'for Producing 1,3-Diols, of which the following is a specification.
' Our invention relates to new rocesses for producin 1,3-dihydroxyl bo ies by the electrolytlc reduction of ketone-alcohols. The ketone alcohols are conveniently prepared by the condensation of ketones with formaldehyde by means of alkaline reagents. Our electrolytic reduction is carried. out in acid medium, using lead, nickel, etc., cath- The reaction proceeds according to the following equation:
CH3.QO.CR2.OH2OH+2H= cmcnonoa cn on where R stands for a hydrogen atom or an organic radical.
In order to illustrate the new process more fully the following example is given: The electrolytic apparatus consists of the usual anode and cathode compartments. The anode li uid is a dilute sulfuric acid solution, pre erablya 10% solution. The cathode liquid consists of a 10% ketone-alcohol solution containing enough sulfuric acid to bring the acid concentration to about 10% of the total solution. The anode consists of an passed thro unattackable material or sheet lead. The cathode is made of clean sheet lead or better a hollow lead spiral, through which water is kept running. The liquids in both chambers are kept at about 15 0., the cathode liquid being stirred during electrolysis. The solution is electrolyzed at a potential difference of about 5-6 volts, and a current density of about 4-5 amperes per 100 square centimeters. There is an excess current h the cell to insure complete reduction. T e cathode liquid is neutralized with sodium carbonate, the water evaporated off in cacao atas-low a temperature as possible, and the glycol is fractioned in 'vacuo. In this way the dihydroxyl bodyis obtained in more than 50% yield of the theoretical.
We claim:
1. The process for'producing 1,3-diols by the electrolytic reduction of ketone-alcohols in acid media.
2. The process for producing 1,3-diols by the electrolytic reduction of ketone-alcohols in dilute sulfuric acid solution using lead electrodes.
In testimony whereof, we afiix our signatures in presence of two witnesses.
LUCAS PETRON KYRIAKIDES. RICHARD BLAIR EARLEL Witnesses: I
M. A. HAGARTY," E. GRACE BROWNE.
US73810412A 1912-12-21 1912-12-21 Process for producing 1,3-diols. Expired - Lifetime US1094224A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2419515A (en) * 1942-12-14 1947-04-22 Phillips Petroleum Co Preparation of 1, 3-butylene glycol
US2422468A (en) * 1942-07-04 1947-06-17 Standard Oil Dev Co Electrolytic production of pinacols

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2422468A (en) * 1942-07-04 1947-06-17 Standard Oil Dev Co Electrolytic production of pinacols
US2419515A (en) * 1942-12-14 1947-04-22 Phillips Petroleum Co Preparation of 1, 3-butylene glycol

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